Reaktion #445194

Reaktionsgleichung

3,3,5-Trimethoxy-2-pyrrolidinone

adenosine 2',3',5'-triacetate

→

N6 -(3,3-dimethoxy-2-oxo-5-pyrrolidinyl)adenosine 2',3',5'-triacetate

Ausbeute 73.4%

Lösungsmittel

benzene acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigereacted
2. 2
   Temperaturto cool

Vorschrift

3,3,5-Trimethoxy-2-pyrrolidinone (445 mg) was evenly admixed with adenosine 2',3',5'-triacetate (1 g) and the mixture was melted and reacted by heating at 160° C. for 2 hours. The reaction mixture was then allowed to cool and subjected to silica gel column chromatography using benzene-acetone (2:1) as the eluent to give N6 -(3,3-dimethoxy-2-oxo-5-pyrrolidinyl)adenosine 2',3',5'-triacetate (1 g). This product was dissolved in ammonia-saturated methanol (30 ml) and left standing at 5° C. for 17 hours, after which time it was concentrated under reduced pressure. The residue was washed with benzene and the insolubles were subjected to silica gel column chromatography using chloroform-methanol (10:1) as the eluent. The active fractions were pooled and concentrated under reduced pressure to give crystals. Recrystallization from methanol-acetone yielded N6 -(3,3-dimethoxy-2-oxo-5-pyrrolidinyl)adenosine as colorless crystals (680 mg).

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